(1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione

• ChemBase ID: 4465
• Molecular Formular: C20H24O10
• Molecular Mass: 424.39856
• Monoisotopic Mass: 424.13694697
• SMILES: C1(=O)O[C@@H]2[C@]([C@@H]1C)([C@@]13[C@]4([C@@]5([C@H](O1)OC(=O)[C@@H]5O)[C@@H](C[C@H]4OC3=O)C(C)(C)C)[C@H]2O)O
• Canonical SMILES: O=C1O[C@@H]2[C@@]([C@@H]1C)(O)[C@@]13[C@]4([C@H]2O)[C@H](OC3=O)C[C@H]([C@@]24[C@H](O1)OC(=O)[C@@H]2O)C(C)(C)C
• InChI: InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10+,11+,15+,17+,18+,19-,20-/m1/s1
• InChIKey: SQOJOAFXDQDRGF-MMQTXUMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione
• IUPAC Traditional name: (1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^{1,11}.0^{3,7}.0^{7,11}.0^{13,17}]nonadecane-5,15,18-trione
• Synonyms: ginkgolide-B

Database IDs

• PubChem SID: 160967897; 99443280
• PubChem CID: 6324617

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.709941
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.5822128
• LogD (pH = 7.4): -0.5822338
• Log P: -0.58221257
• Molar Refractivity: 91.382 cm^3
• Polarizability: 38.405952 Å^3
• Polar Surface Area: 148.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.49
• LOG S: -1.91
• Solubility (Water): 5.21e+00 g/l

DETAILS

DrugBank - DB06744

• Drug Groups: nutraceutical
• References: Wang SJ, Chen HH: Ginkgolide B, a constituent of Ginkgo biloba, facilitates glutamate exocytosis from rat hippocampal nerve terminals. Eur J Pharmacol. 2005 May 9;514(2-3):141-9. [Pubmed]

REFERENCES

• Wang SJ, Chen HH: Ginkgolide B, a constituent of Ginkgo biloba, facilitates glutamate exocytosis from rat hippocampal nerve terminals. Eur J Pharmacol. 2005 May 9;514(2-3):141-9. Pubmed